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Pregled bibliografske jedinice broj: 878683


Autori: Uzelac, Lidija; Škalamera, Đani; Mlinarić- Majerski, Kata; Basarić, Nikola; Kralj, Marijeta
Naslov: Selective photocytotoxicity of anthrols on cancer stem-like cells: the effect of quinone methides or reactive oxygen species
Izvornik: European journal of medicinal chemistry (0223-5234) 137 (2017); 558-574
Vrsta rada: članak
Ključne riječi: antiproliferative activity, cancer stem cells, photodehydration, quinone methides, reactive oxygen species, singlet oxygen
Cancer stem cells (CSCs) are a subpopulation of cancer cells that share properties of embryonic stem cells like pluripotency and self-renewal and show increased resistance to chemo- and radiotherapy. Targeting CSC, rather than cancer cells in general, is a novel and promising strategy for cancer treatment. Novel therapeutic approaches, such as photodynamic therapy (PDT) have been investigated. A promising group of phototherapeutic agents are reactive intermediates - quinone methides (QMs). This study describes preparation of QM precursor, 2-hydroxy-3- hydroxymethylanthracene (2) and a detailed photochemical and photobiological investigation on similar anthracene derivatives 3 and 4. Upon photoexcitation with near visible light at λ > 400 nm 1 and 2 give QMs, that were detected by laser flash photolysis and their reactivity with nucleophiles has been demonstrated in the preparative irradiation experiments where the corresponding adducts were isolated and characterized. 3 and 4 cannot undergo photodehydration and deliver QM, but lead to the formation of phenoxyl radical and singlet oxygen, respectively. The activity of 1-4 was tested on a panel of human tumor cell lines, while special attention was devoted to demonstrate their potential selectivity towards the cells with CSC- like properties (HMLEshEcad). Upon the irradiation of cell lines treated with 1-4, an enhancement of antiproliferative activity was demonstrated, but the DNA was not the target molecule. Confocal microscopy revealed that these compounds entered the cell and, upon irradiation, reacted with cellular membranes. Our experiments demonstrated moderate selectivity of 2 and 4 towards CSC-like cells, while necrosis was shown to be a dominant cell death mechanism. Especially interesting was the selectivity of 4 that produced higher levels of ROS in CSC-like cells, which forms the basis for further research on cancer phototherapy, as well as for the elucidation of the underlying mechanism of the observed CSC selectivity based on oxidative stress activation.
Projekt / tema: HRZZ-IP-2013-11-5660, HRZZ-IP-2014-09-6312
Izvorni jezik: ENG
Rad je indeksiran u
bazama podataka:
Current Contents Connect (CCC)
Science Citation Index Expanded (SCI-EXP) (sastavni dio Web of Science Core Collectiona)
Kategorija: Znanstveni
Znanstvena područja:
Kemija,Kliničke medicinske znanosti
URL Internet adrese:
Broj citata:
DOI: 10.1016/j.ejmech.2017.05.063
URL cjelovitog teksta:
Google Scholar: Selective photocytotoxicity of anthrols on cancer stem-like cells: the effect of quinone methides or reactive oxygen species
Upisao u CROSBI: Enidija Lukša (, 1. Lip. 2017. u 12:13 sati

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